Optically active alpha-amino acids and derivatives thereof are widely used in living bodies. Recently, a method of synthesizing an amino acid through a phase transfer reaction using a quaternary ammonium salt as a phase transfer catalyst has attracted great attention as a synthesis method for mass production of these. In particular, by using an ammonium salt derived from a chiral alkaloid as a catalyst, asymmetric synthesis of an optically active alpha-amino acid has become possible. M. J. O'Donnell first reported an asymmetric synthesis method for alpha-amino acids using a compound of Formula A as a chiral phase-transfer catalyst, which is a tetraalkylammonium halide derived from a cinchona alkaloid, which is a chiral alkaloid (O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353). However, in the reaction using the compound of the following formula A as a catalyst, the alpha-amino acid product has an optical purity of only about 80% ee, which has a limitation in terms of mass production.

Lygo group [Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595.] and Corey Group [Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.] developed a compound of Formula B as seen below which was a new cinchona alkaloid-based catalyst, and synthesized asymmetric alpha-amino acids through alkylation using the compound as a phase transfer catalyst. Thereafter, Lygo group and Corey group faced an economic issue of high production cost, and because the temperature condition for the alpha-amino acid synthesis was −78° C., its practical industrial application was limited.

Moreover, the Park Group [Park, H.-G.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-K.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-S. Angew. Chem. Int. Ed. 2002, 41, 3036.] developed a catalyst of Formula C as seen below, asymmetrically synthesized alpha-amino acids using the catalyst as a phase transfer catalyst, but the reaction needed 5 mol % of the catalyst, 5 equivalents of a reaction reagent, and the reaction temperature had to be maintained at 0° C., thus making industrial application difficult.

Under these circumstances, research on the development of a novel chiral phase-transfer catalyst capable of asymmetrically synthesizing alpha-amino acids with high optical purity under industrially applicable reaction conditions has been actively carried out, but it is still inadequate.